The Midlife Vices of Greg Giraldo

About six years ago, comedian Jesse Joyce — a man who, I can tell you from personal experience, could talk intelligently about politics, polish off six pints of ale at a fairly rapid clip, and continue making his articulate points as if he had simply downed a glass of cherry cola — decided that maybe this sort of drinking wasn’t healthy, and gave it up.

Around the same time, another comedian with a tendency for overindulgence, veteran comic and former attorney Greg Giraldo, made a similar decision for himself. The pair shared a manager, and that manager suggested that the two comics work together, since they could theoretically help each other navigate this new road of sobriety.

The two became fast friends, and for the next five years, Joyce came to regard Giraldo as an older brother, becoming his opener on the road, and his writing partner on the Comedy Central roasts that would greatly increase Giraldo’s public profile. The two would speak virtually every day, except on days when Giraldo was otherwise occupied. Because while Joyce remained sober, Giraldo did not.

“I was always disappointed after we’d have, like, a month where everything was great,” says Joyce. “I always knew, because he would cut off contact with me for a couple of days. We would talk every day, and then there’d be a period of a couple of days when he wouldn’t get back to me, and I would just know. I’d have this little sinking feeling, and then it got less and less disappointing because it would happen so many times. Then it was just like, well, that’s probably what’s happening again.”

Sadly, Joyce says he was not surprised when Greg Giraldo died this past September, at the age of 44.

The much-beloved comedian left behind three sons, and such was the admiration for Giraldo that some of the top names in comedy — including Jerry Seinfeld, Lewis Black, Dave Attell, Colin Quinn, Jim Norton, Judy Gold, and Ted Alexandro — will gather at the Beacon Theater for a benefit for his boys on Wednesday, February 9.

The cause of Giraldo’s death was an accidental overdose of prescription drugs after a gig at a comedy club in New Jersey called the Stress Factory, but Giraldo had been spiraling for years. While there’s no way to know what goes on inside someone else’s mind — possibly more so for addicts — when it comes to Greg Giraldo, Joyce, who’ll also perform at the benefit, has his theories.

The word “brilliant” isn’t thrown around the comedy scene too often, but it may have applied more than most to Giraldo. He was a Columbia and Harvard Law School graduate who waded into the world of law, but just couldn’t make himself care about legal minutiae and corporate profits, taking refuge instead in the world of jokes, where his natural combination of brains and street smarts manifested in comedy that was, at times, an unusual blend of cerebral and populist.

In his 2009 CD and DVD, the now ironically-titled Midlife Vices, Giraldo touched on his two divorces and his drinking and drug use. In one routine about how the drinking age should be forty because that’s when you really need to be drunk, he casually mentioned his alcoholism and how his life at the time was so much harder than it had been in his teens, and how now, he wanted to be fucked up all the time. But in addition to his personal candor, he examined the state of our world in hilarious fashion, including a remarkably nuanced and yet never hectoring segment on the folly of ethanol — into which he managed a firmly-in-context “pussy waxing” reference — and comedic treatises on the manipulation of race in the 2008 election, our nation’s plunge into obesity, the importance of stem cell research, the loss of the U.S. manufacturing sector to China, and a dual rip on the pathetic trend of theme restaurant employees singing “Happy Birthday” to adults and the nonsensical aspects of certain anti-immigration arguments.

Comedian Jim Norton knew Giraldo for about fourteen years, including several where they worked together on Tough Crowd with Colin Quinn. Norton says that whether on that show or in the no-holds-barred behind-the-scenes world of Greenwich Village’s Comedy Cellar, where comics who’ve known each other for years wait for their sets at the restaurant upstairs, joking and bantering and brutally ripping on each other in a sort of cruder, more feral Algonquin Round Table, Giraldo’s intellectual superiority was always apparent.

“He was a very fierce opponent,” says Norton. “You would never realize that Greg was as hard-hitting as he was unless you fucked with him. He had a very, very fast mind, which meant he was very hard to argue with, because on top of being funny, his mind would adjust very quickly. We used to always talk politics at the Cellar, and in a political discussion he always knew what he was talking about. If you had a good point, he always had something just as smart or smarter to counter you with. He was a really brilliant guy.”

“Outside of being a comic, he was a genius as a person,” says Joyce. “He went to Columbia and Harvard at the top of his classes. That dude could explain to you the root cause of the Boer War for forty-five minutes. He just knew everything.”

What made Giraldo’s comedy so hard-hitting and relatable, though, was not just his smarts, but a fearlessness that evolved over time, allowing him to confront head-on the worst of what he saw both in himself, and in the world around him.

“There’s a lot of really smart guys that are afraid of offending,” says Norton, “and a lot of ballsy guys that are just dopes. But he had a brilliant comic mind, and he was completely unafraid on stage. That’s what I loved about watching him. I knew that I was never gonna hear anything sold softly.”

“He was so confident on stage, such a master of words and so naturally funny, that he could take anything he wanted to talk about and make it funny even if you disagreed with his politics on it. At the end of the bit, it was flawless logic,” says Joyce. “You could disagree with the concept of gay marriage, but he would [talk about this] in Texas, or in the South. We’d work together in Georgia, and he would start the bit with some version of, ‘if you think gay people choose to be gay, you’re an asshole.’ He would confront people aggressively to say, what you believe is wrong. But by the end of the bit, not only would he get an applause break, but everybody would be like, ‘Huh. I see your point.” He could take anything he believed in, and make it funny to people who disagreed with him.”

But an intelligence that pronounced can be its own burden, and Joyce believes it was this very gift that made Giraldo’s struggle with addiction so perilous.

“My theory is, he was too smart for his own good,” he says. “Because he was so brilliant, he could outthink everything. He thought it was enough to know everything about a thing without actually living it.”

Joyce says that Giraldo knew the theories and practices of sobriety possibly better than anyone, but allowed himself to believe that with knowledge that great, he could forgo the actual practice.

“He could always out-argue his own mind, especially since he was a lawyer,” says Joyce. “He could easily come up with thirty reasons to stay sober tonight, or thirty reasons to get ripped drunk and ruin a bunch of things. He could talk himself into either.”

This gave the “older brother” aspect of their relationship a unique tilt, as in addition to learning great things from Giraldo about comedy and life, Joyce learned just as much about what not to do.

“I was on my way to getting married,” says Joyce, “and he gave the greatest advice of anybody I’ve ever met that he could never apply to himself. Now I’m married, but at the time she was my girlfriend, and we’d get into a fight on the phone. I’d go bitching to Greg about it, and he had this perfect insight, like, ‘she’s doing that because of this, and here’s what you gotta do,’ and he’d be dead on. I’d be like, ‘you’re totally right.’ And then I’d go, ‘Wait a minute. Aren’t you twice divorced? What the fuck do you know about it?’ He had the most disastrous relationships, and he gave the greatest advice ever. That’s the paradox that was so fascinating. He gave the greatest advice about women, and he just had a string of crazy relationships. And he could give great sobriety advice, yet couldn’t stay sober.”

Once Giraldo became a hit on the Comedy Central roasts, the natural drive of an addict and Giraldo’s rationalizations began to mix with the perils of fame. On the road, he not only found the party — and the alcohol and drugs that came with it — every time, but danger began to seek him out.

“I remember [when I was drinking], I would do this all the time,” says Joyce. “I would go, ‘man, there’s a lot of drunks’ wherever I was, Birmingham, AL or wherever. ‘There’s a ton of drunks here.’ And it was like, no. There are no more here than there were anywhere else. But I sought those people out. I kind of had this sign around my neck, and we gravitated toward each other. And that’s what would happen to Greg. We’d go on the road, and some sketchy blow dealer with a nickname like R2-D2 would come to the show. And he would immediately come over, because he got the vibe that this was the guy to talk to. I feel like the business at large enabled him in that way.”

Joyce says that the two would seek out ways to stay busy in their mutual battle for sobriety, but that surrounded by constant temptation, Giraldo found it harder and harder to fight.

“People were just offering it all the time,” says Joyce. “The irony is that for those people, for the guy in Tulsa, OK, he goes out and drinks an entire bottle of Jack, but he does that once. Then, for the rest of the year, he goes, ‘I got super ripped with this comic who was in town!’ For a lot of those people, that’s like the strip club DJ’s one experience doing blow with a celebrity. But for Greg, he’d find that guy in every town.”

In time, finding wild parties became something of a badge of honor for Giraldo as well.

“He structured so much around that persona that maybe he was afraid of, is anybody gonna think I’m cool and worth seeing if I’m not kind of a badass. That was the number one argument we would always have,” says Joyce. “We were very like-minded in this way. I really liked waking up in a hotel with a half-lit cigarette in my mouth in the morning, drinking a bottle of Jack. I like that lifestyle. I’m that guy. But it was killing me, and I found a way to kind of trick myself in sobriety, by [thinking], I used to be that guy, and that’s actually more badass. I did all that. I wear it like a badge of courage that I ruined a lot of shit and drunk-drove across four states in a blackout, but I’m very proud of the fact that that’s who I used to be. So I would always say to Greg, ‘why can’t you rest on that? Why can’t you be thrilled that you used to get blasted with Pantera in the woods?’ We went to some party in a mansion in the side of a mountain way out somewhere in Arizona, where it was all strippers and Ketamine, just craziness, and it was like, why can’t you be excited that you have those stories? Why do you need to keep making more? Because the number of awesome stories you have is, these days, really being outweighed by the number of shitty stories you have. Because that’s what always ends up happening. You have these rose-colored glasses about how great it is, but it gets less and less great, and you have to drink and do more and more substances to try to recreate the good times on the road.”

For people in the comedy world as well as many of Giraldo’s fans, his struggles were no secret, and his openness about it is part of what made him great as a comic.

But this knowledge of Giraldo’s struggles also meant that those around him lived with a sad sense of helplessness, watching a friend spiral downward while powerless to prevent it.

“We knew he had his troubles and that he was struggling with certain things, and it was kinda hard to watch,” says Norton. “In the last three years or so, it became more and more apparent that he was struggling. I would say to him, ‘hey man, did you relapse?’ We would talk about sobriety, and when he wanted to talk to me about it I felt he would. But I didn’t know at any given moment if he was just sad in general, or using. I just knew that he was hurting.”

“What’s so insidious about addiction,” says Joyce, “is that it tricks you — and everyone around you — into thinking that this is the way it is for now, but that it’s gonna get better. Because we would have these periods of time where it was all fine and great, and I would get lulled into the idea that maybe this time it’ll stick. For me, I know I always have that option. I can always go out and get drunk tomorrow if I want and see where that takes me, get back on that elevator and ride it down a few more floors, but my life has improved enough for me to know that that was the problem. I don’t think Greg ever gave it enough time. He would get inklings of it. He’d start getting up earlier in the morning and read the paper. He would do proactive, productive things, and be on time for flights and stuff. And he’d go, ‘yeah, this is great.’ But I don’t think he ever gave it enough time to really reap the benefits of sobriety.”

It would be wonderful if there was some lesson to be taken from the loss of Greg Giraldo — don’t do drugs, kids — but the realities of addiction are far too complex. So instead of a lesson, we have a legacy: his material, and the enjoyment we got — and still can get — from watching Greg Giraldo do the one thing it seems that he was put on this planet to do: be really fucking funny.

Trying to figure out anything else is just folly.

“[Greg’s death was] simultaneously the most and least surprising thing I’ve ever experienced,” says Joyce. “I knew it was gonna happen. I just didn’t know it was gonna be that weekend. That’s what surprised me. Like, really? At the fucking Stress Factory? He and I had done the Stress Factory a dozen times. I remember vividly the last time we were there, like, I [would have] wanted to turn to him in the car and said, ‘that’s it. That’s where you’re going out in a blaze of glory. The Stress Factory.’ The point being, given the rock star lifestyle, how underwhelming that wound up being. If he told me that he was going on tour with Korn or something like that, and they were gonna be traveling around Amsterdam, that, to me, would have been like, ‘oh, OK. That’s probably where he’ll die.’ But that’s the reality of addiction. It happens on a Tuesday.”

Larry Getlen is a freelance writer in Brooklyn who regularly contributes to the New York Post and others.